Romantic Holiday Films

Can’t decide which movie you and your date should watch together? These eight holiday-themed love stories will put you both in the spirit to celebrate romance — and the season.

By Diane Mapesating can be tough during the winter. Everything is cold, wet and blustery (including the people), plus you’re so busy shopping, cooking and wrapping gifts that it’s hard to squeeze in a night out on the town. Luckily, it’s incredibly easy to cuddle up on the couch with a warm date, a delicious drink and a warm and fuzzy holiday romance.

“I think we all want to be happy at the holidays,” says Tina B. Tessina, psychotherapist

and author of The Unofficial Guide to Dating Again. “We want to escape whatever difficulty is in our reality, and romance provides an emotional holiday.”

Below, we’ve listed our top picks for romantic holiday films that not only offer a lovely escape from your seasonal stress, they’ll also help you and your date grow closer (and avoid the blustery winter winds!) while spending a night chilling on the couch together:

8. Four Christmases (2008)
Unmarried partners Brad and Kate (Vince Vaughn and Reese Witherspoon) have successfully managed to escape sharing their families (and accompanying secrets) for three consecutive holiday seasons before finding themselves being forced to visit all four parents in a single day. The holiday visiting marathon nearly causes the couple to split up, but instead, both Brad and Kate finally realize why they’re madly in love with each other — warts and all.

What makes it a great love story: Tess M., a 39-year-old accountant from Seattle, WA, says that she likes this film for its realistic portrayal of modern families and their impact on people’s romantic relationships. “Everybody has some deranged hidden relative or a family secret that they don’t want getting out,” Tess explains. “In this movie, their families are very strange, and the couple avoids them because otherwise, things get revealed. They’ve hidden who they are.” Hiding your true self from your partner isn’t a good relationship strategy, though, as the movie ultimately reveals. As Tess says, “when the skeletons are released from the closet, if you like someone, you’ll remain together.”

7. Holiday Inn (1942)
Jim Hardy (Bing Crosby) and Ted Hanover (Fred Astaire) are a successful nightclub song-and-dance duo grappling with romance and rivalry issues while they perform at a New England inn that’s only open during the holidays. Thanks to the success of one of the songs featured on its soundtrack, this film was loosely remade as White Christmas in 1954 — only this time, it was filmed in Technicolor and with Danny Kaye taking over the second lead spot after Astaire turned it down.

What makes it a great love story: Tess M. picked Holiday Inn as one of her favorite holiday romances because of the old-fashioned dating dynamic portrayed in the film. “These men want something so much that it’s worth fighting for,” says Tess. “They put their egos on the line. It’s worth risking being made a fool of for something that they’re interested in — or, rather, someone they were interested in. Back then, a suitor’s temperament was different. Nowadays, men are like, ‘eh, whatever,’” she shrugs.

6. The Bishop’s Wife (1948)
In this film, Cary Grant plays an angel named Dudley who comes to Earth at Christmastime in order to answer the prayers of workaholic bishop Henry Brougham (played by David Niven). Once there, Dudley falls for Henry’s unhappy, neglected and positively luminous wife, Julia (played by Loretta Young). Despite this complication, Dudley still manages to fulfill his angelic duties, such as teaching Henry the importance of appreciating the little things in his life.

What makes it a great love story: The image of suaveness personified, Grant’s portrayal of Dudley makes him the perfect suitor, as he’s completely safe and incapable of sin (or sex). But Dudley still “makes love” to Julia (in the traditional sense) by showering her with compliments, attention and a few innocent temptations (like ice skating). As a result, you get a fun fantasy about a woman who gets to have her beefcake and eat it, too — at least for a few sweet moments. Prefer your angels to be a bit more modern? Then check out The Preacher’s Wife, a 1996 remake starring Denzel Washington and Whitney Houston.

with a penchant for alcohol, cigarettes and charming heels, tries to improve herself over the course of a year by tracking her love life and related sundry adventures in a diary.

What makes it a great love story: This contemporary retelling of Pride and Prejudice gives audiences an extremely relatable protagonist who’s fumbling and bumbling her way through life — and love — like many of us do, eventually succeeding in both. “Singletons” are celebrated, while “smug marrieds” get called out. And along with lots of laughs (and some dazzlingly awful holiday sweaters), we get to watch two scrumptious hunks (played by Hugh Grant and Colin Firth) fighting for the title character’s affections.

4. The Holiday (2006)
Hollywood exec Amanda Woods (Cameron Diaz) and British newspaper editor Iris Simpkins (Kate Winslet) are both heartbroken women who decide to swap homes for the holidays in order to get away from it all. Amanda promptly gets entangled with Iris’s handsome widowed brother (Jude Law), while Iris becomes involved with two different men: elderly screenwriter Arthur (Eli Wallach), who teaches her the ins and outs of romantic comedy, and composer Miles (Jack Black), with whom sparks soon start flying.

What makes it a great love story: When it comes to romance, this movie delivers by intertwining six different love stories for the price of one movie rental. We’re given insight into old loves, the promise of new loves, plus a few tragically lost loves along the way (and the hope that losing a soul mate doesn’t mean you’re destined to be single for the rest of your life). Plus, we get to witness the sweet friendship that develops between Iris and Arthur, which serves as a delightful holiday reminder that love isn’t just about dating and mating exclusively.

3. An Affair to Remember (1957)
Cary Grant (yes, him again!) and Deborah Kerr play lovers Nickie Ferrante and Terry McKay, who are separated thanks to the cruel vagaries of fate (and the dangers of jaywalking). Once the couple is reunited on Christmas Eve, they realize that they’re still crazy for each other. In the end, love conquers all — including a few traumatic injuries.

What makes it a great love story: Richard L., who works in the hospitality industry in Walla Walla, WA, calls this three-hankie holiday classic “the ultimate love story.” “Romance doesn’t get any better than this,” he enthuses. “Her love was so big that she didn’t want to put him through her tragedy.” The theme of sacrifice plays a huge role in this film (as it does in another seasonal favorite, O. Henry’s The Gift of the Magi). First, Nickie and Terry agree to part for six months so they can disentangle themselves from other relationships, then Terry refuses to tell Nickie that she was struck by a car and paralyzed while running to get to their planned reunion on top of the Empire State Building. An Affair to Remember is also the gift that keeps on giving; in addition to three different screen versions (1965’s Bollywood adaptation, Bheegi Raat, and 1994’s Love Affair, starring Warren Beatty and Annette Bening), the plot of this film inspired yet another unforgettable romance decades later that still resonates today: 1993’s Sleepless in Seattle, starring Tom Hanks and Meg Ryan.

2. It’s a Wonderful Life (1946)
Troubled, suicidal George Bailey (Jimmy Stewart) is saved by an angel (Henry Travers) on Christmas Eve, who goes on to show him how much he’s actually contributed to the lives and loves of others in his hometown of Bedford Falls, New York.

What makes it a great love story: The powerful love between George and Mary Bailey (played by Donna Reed) forms the backbone of this bittersweet classic holiday staple. Their romance starts out with a childhood crush (who can forget Mary whispering “George Bailey, I’ll love you ‘til the day I die” into his bad ear?) and carries on through their courtship as young adults (the telephone scene is still a sizzler), subsequent marriage, and the maelstrom that follows.

1. Love Actually (2003)
Set in London, this series of star-studded vignettes tells the story of nearly two dozen people — some falling in love, others mourning a heartbreaking loss, yet still others determined not to let it slip away — during the frantic five weeks before the Christmas holiday.

What makes it a great love story: Richard L., who calls himself a hopeless romantic, says this is his #1 holiday pick because it includes a series of love stories, but they’re not the typical ones you find in most romantic comedies. “What’s really interesting is that it covers all kinds of love,” he asserts. “You’ve got parental love, brotherly love, romantic love, unrequited love… plus you’ve got friendship, too. It’s a series of brilliantly written vignettes that ultimately get tied together in a wonderful way.”
Diane Mapes is a freelance writer based in Seattle and the author ofHow to Date in a Post-Dating World. She can be reached via her Web site,dianemapes.net.